As someone who learned on python (many years ago), I think the balance of being allowed to shoot myself in the foot, while only having to learn complexity when complex concepts came up, was a good combination rather than a bad one. Trying to learn C++ and Java before, having to type everything was an impedement. On python, you find out that types still matter when you try to add a string to an integer, for example. The moment the type matters to you is when you need to dig into those details. I'm not sure I would have the career I do if it hadn't been around to be the one language that fit my 16-year old brain.